Marriages don’t deteriorate overnight. There’s often a gradual decline, sometimes over years or decades, that leads to an eventual breaking point and makes divorce inevitable.

We asked now-divorced men to reveal the moment that signaled their marriages were finally over for good. Here’s what they said:

1. When my son mentioned ‘mommy’s new friend.’

“I should have known it was over when she said at dinner that she didn’t know whether she loved me anymore. I should have known it after 18 months of sleeping in separate bedrooms. I should have known it when she stopped demonstrating any positive or negative emotions toward me. I should have known it after spending a holiday weekend with our young son on a road trip that she declined to take with us. I should have known it after I saw her missing wedding ring upon returning home from that trip. I should have known it when she moved out the next day, driving away with our little boy in the back seat. But I didn’t. Still, I hoped. And then, two weeks later, my son innocently mentioned a dog and some little girls he had been playing with. They belonged to ‘mommy’s new friend.’

‘Did you have a sleepover at mommy’s new friend’s house?’